Fifty Years Apart, Thirty Miles Together
- Richard Webster
- Jul 16
- 3 min read
Ken expected a 30-mile training ride this morning. What he got was something better: a chance to share the road with his second-oldest grandson, Jacob.
With just 21 days left before Ken begins his nearly 600-mile ride around Lake Michigan, every training mile matters. But some miles mean more than fitness, and today proved it.
Ken introduces the July 16 ride and the special training partner joining him for the morning.
A Beautiful Morning, With One Concern
The ride began at a comfortable 67 degrees. The morning was quiet, the roads were calm, and the sun was trying to break through. But the soft orange glow in the sky was not ordinary cloud cover. Smoke from wildfires farther north had settled into the area, leaving a visible haze over the route.
Ken kept an eye on the conditions and was prepared to turn around if either rider had trouble. Health and safety come before training miles, especially with a much longer journey approaching.
The morning sun appears through the wildfire haze as Ken explains the plan for the ride.
Jacob joins his grandfather for a 30-mile training ride through the Wisconsin countryside.
Ken and Jacob pause together along a road softened by the morning haze.
The Climb to Holy Hill
Their destination was Holy Hill, a familiar landmark in Ken's training and a place that always makes the miles feel worthwhile. Getting there meant taking on plenty of rolling terrain and a demanding final climb.
Jacob rode an e-bike, but that did not make the hills disappear. He estimated that the route included roughly 1,700 feet of climbing. At the top, he had nothing but respect for how his grandfather handled it.
“He got through it like a champ,” Jacob said after the ride.
Ken and Jacob reach Holy Hill together after the morning's biggest climbs.
A Wisconsin Traffic Jam
Not every obstacle came in the form of a hill. At one point, a group of geese decided the road belonged to them.
Ken offered some friendly encouragement from behind the handlebars. Eventually, the flock cleared the way and the riders continued toward home.
Ken negotiates a brief right-of-way disagreement with some local geese.
The Home Stretch
By the final few miles, the cool start had warmed to 82 degrees. Ken and Jacob arrived home around 10:30 that morning, tired, warm, and still moving forward.
The riders enter the home stretch after hours on the road.
With about three miles remaining, the goal was simple: keep pedaling and finish together.
What the Numbers Do Not Show
The final total was 30.36 miles in 3 hours, 55 minutes, and 35 seconds of riding time, with 1,529 calories burned.
Those numbers tell us how far they traveled. They do not tell us what it meant for a grandfather and grandson, nearly 50 years apart, to share the same road, take on the same hills, laugh at the same geese, and arrive home with a story they will both remember.
The July 16 training route through the Holy Hill area.
The final numbers from Ken and Jacob's 30.36-mile ride.
Afterward, Jacob said he would do it again. He also made one thing clear: Ken's progress is not accidental. It is the result of nearly a year of steady training and a willingness to keep preparing, one ride at a time.
Ken and Jacob look back on the hills, the smoke, the wildlife, and what made the day special.
Twenty-One Days To Go
Ken's Lake Michigan journey begins August 6. He is training for nearly 600 miles, but the purpose reaches far beyond the road.
The ride is raising funds for the shipping and handling of Operation Christmas Child shoebox gifts. It costs approximately $10 to send one shoebox, and the goal is to raise $6,000 to help send 600 boxes to children around the world.
No gift is too big or too small. Every contribution helps move another shoebox closer to a child, and together those gifts can grow into something much larger than any one person could accomplish alone.
Help Encourage Ken
The support people leave along the way matters more than they may realize. Please leave Ken a comment below, and when you see this story on Facebook, go back and like or comment there too. Ken reads the encouragement, and it gives him another reason to keep pedaling on the difficult days.
Follow along as Ken prepares, then return during the trip for daily updates, photos, videos, and progress from the road.
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